If you’re energetic and have experience leading a successful field or outside sales team, this could be the role for you! This is a hybrid position supporting our Headquarters in Lake Oswego, OR, working closely with our Territory Managers (TMs) and broader sales organization. We’re looking for an outcome-driven, high-impact leader who is eager to join client meetings, actively assist with closing calls, and provide real-time coaching to increase outbound calling performance and demonstrate what success looks like in managing a full-cycle sales territory, overcoming objections, and securing high-value SaaS contracts.

This role partners closely with Sales and Marketing leadership to drive net-new revenue growth, expand market share within designated regions, and consistently improve win rates. This position reports directly to the Director of Acquisition Sales and plays a critical role in developing our territory sales talent.

This is a hybrid role based at our HQ in Lake Oswego, OR. The schedule is Monday and Friday remote, with Tuesday through Thursday onsite.

Here is more of what you’ll get to do:

• Motivate, train, and coach Territory Managers to meet and exceed monthly, quarterly, and annual revenue goals.
• Drive outbound prospecting performance, coaching the team on high-impact phone skills, hook strategies, and building a robust, self-generated pipeline within their territories.
• Lead from the front by jumping on critical closing calls, helping TMs navigate late-stage negotiations, handle complex objections, and push deals across the finish line.
• Actively participate in virtual and on-site client presentations, pipeline reviews, and hands-on deal strategy to accelerate the sales cycle.
• Develop and implement best practices for full-cycle territory management, account mapping, and consultative value-selling to dealerships.
• Partner with Sales Operations and Marketing to optimize territory assignments, align on regional campaigns, and identify untapped market opportunities.
• Attract, interview, and onboard top-tier sales talent to scale the territory team while actively focusing on continuous talent development and career progression.
• Review customer presentations and discovery calls (via Gong) to provide consistent, actionable feedback that shortens sales cycles and improves closing ratios.
• Track, analyze, and report on key metrics, including regional quota attainment, sales velocity, pipeline health, and conversion rates to drive data-informed decisions.
• Enhance processes, tools, and workflows to maximize territory coverage and efficiency.
• Maintain accountability across the team, including performance management, forecasting accuracy, and productivity expectations.
• Demonstrated ability to work effectively in a mixed mode (onsite, remote or hybrid) environment, including consistent use of video conferencing, collaboration tools, and proactive communication practices while maintaining a professional on-camera presence

You’ll thrive in this role if you have:

• 3+ years of B2B Sales Management experience, specifically managing full-cycle quota-carrying reps (preferably within SaaS or digital marketing).
• Experience in the automotive/powersports space or direct experience selling B2B products to dealerships is a major plus (Bonus qualification).
• A proven track record of driving outcomes—you are relentlessly focused on execution, target attainment, and moving metrics rather than just managing activities.
• Proven experience coaching outbound sales tactics, including phone scripts, handling gatekeepers, and turning cold outreach into qualified opportunities.
• Proven experience coaching and developing a remote or regional team of 10+ Territory Managers through 1:1 mentorship and structured sales methodology training.
• Strong closing instincts with a willingness to roll up your sleeves, hope on a call, hop on a plane to attend a tradeshow, and help your team secure the "win" on major accounts.
• A passion for territory strategy, consultative selling, and building scalable revenue growth models.
• Demonstrated success collaborating cross-functionally with internal teams and building strong relationships with dealership decision-makers.
• Strong systems orientation with experience using CRM platforms (Salesforce), Jiminny (Similar to Gong).
• Excellent organizational, communication, and people leadership skills with the ability to manage a geographically dispersed team.

Employee benefits & earnings:

• Full Coverage Health Insurance
• Company 401K Match
• Life Insurance (Basic and Voluntary)
• Open & Flexible Vacation Policy (including sick leave)
• Generous Leave Benefits: medical, maternity, paternity, and personal
• Competitive base salary plus commission
• Top performers qualify for our annual President’s Club trip, along with additional incentives and compensation growth opportunities

Does this position sound like something you would enjoy and be successful at, but you’re not sure you have the exact qualifications to be considered? While our job descriptions are an outline for the type of candidate we’re looking for, it is not a checklist. We encourage you to apply!

*This role is not open to candidates located in Colorado, Connecticut, California, Maryland, Nevada, New York, Rhode Island, or Washington.

Who is LeadVenture? LeadVenture is the market-leading SaaS provider of digital retailing, eCommerce, digital marketing and eCatalog solutions for dealerships across 12 industry verticals including power-sports, marine, RV, pre-owned auto, agriculture and more. Our family of brands includes Dealer Spike, Dealer Car Search, Frazer, TCS Technologies, Net Driven, Direct Communications, Inc. (DCi), Powersports Support, Level 5 Advertising, PSM Marketing, Monroney Labels and Interact RV. Each one is an industry leader in driving consumer engagement and maximizing lead generation for dealers. Our investors include the private equity firms True Wind Capital and TA Associates.

LeadVenture provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability or genetics. In addition to federal law requirements, LeadVenture complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, transfer, leaves of absence, compensation, and training.

LeadVenture expressly prohibits any form of workplace harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of LeadVenture employees to perform their job duties may result in discipline up to and including discharge.

Pay: $75,000.00 - $155,000.00 per year

Benefits:

• 401(k) matching
• Dental insurance
• Paid time off
• Vision insurance

Application Question(s):

• Have you directly managed a team of 10+ reps? (Yes/No)
• Do you have hands-on experience coaching outbound prospecting (cold calling/lead gen)? (Yes/No)
• Are you able to work onsite Tuesday–Thursday in Lake Oswego, OR from 7:00 AM – 4:00 PM?
• Do you have 3+ years managing a B2B sales team (AE/TM, inside sales)? (Yes/No)

Work Location: Hybrid remote in Lake Oswego, OR 97035